Ah, the holidays. A magical time of twinkling lights, endless parties, and cozy nights by the fire… until someone asks, “So, who are you bringing to the party?” or “When are you settling down?” Suddenly, the holidays feel less like a Hallmark movie and more like an Olympic event…

So, how do you survive this holiday dating season without losing your mind—or your heart? Fear not, because I’ve got your back with the ultimate Holiday Dating Survival Guide. From dealing with last-minute date plans to keeping those conversations going at parties, managing the plus one pressure like a pro, or navigating the holiday hookup, here’s everything you need to know to get through this season. Grab a glass of wine, and let’s dive in..

Survival Tip #1: Manage the Plus-One Pressure Like a Pro

Ah, the dreaded “Who’s your plus one?” question. Cue eye roll. It’s the worst, right? This question can feel like a snowball hurtling straight at your face when you’re still single or haven’t found the right person yet. But, please.. don’t let it stress you out! If you’re flying solo, rock it. Own that invitation and strut in like you're the life of the party (because, let’s be real, you are). And hey, if you’re really feeling the plus one pressure, grab a fun friend to join you. A great wing-person can ease any nerves and make any (and every) party a blast.

But if you are looking for love and connection this season, consider this: the holidays are the perfect time to meet someone new. The festive energy, the cozy vibes, and the endless stream of parties make it a great opportunity to connect with a special someone. And don’t forget: First Round’s On Me makes it easier than ever to cut through the small talk and get straight to meeting IRL—no endless texting or awkward “Hey, what’s up?” chats. Just a beautifully intentional date request, and you’re good to go. 

Survival Tip #2: The Art of Surviving Family Interrogations

Families mean well (usually), but their curiosity can feel like a cross-examination. “When are you settling down?” “What happened to that nice person you were seeing?”

What to Do: Have a Plan, Keep your responses lighthearted but firm. “I’m focusing on myself right now!” or “The right person hasn’t found me yet—they must be stuck in traffic!” Redirect ing the Conversation is always a great way to skirt around those subjects, so ask about their hobbies, their favorite holiday recipes, or anything that steers the topic away from your love life. Also there is nothing wrong with taking a break . Step outside, grab a drink, or play with a dog if things get overwhelming.

Pro Tip: If all else fails, mention First Round’s On Me (FROM). Say you’re dating with intention and trying a modern, no-nonsense approach to meeting people. It’s the perfect way to both shut them up and sound like you’ve got things under control.

Survival Tip #3: How to Keep the Conversation Festive Without Getting Stuck in the "So, What Do You Do?" Rut

We've all been there: the holiday gathering conversation. “So, what do you do?” “Any fun plans for the new year?” Cue the painfully awkward responses and the inevitable moment when someone spills their drink because they’re bored out of their minds. Here’s how to spice things up: ditch the basics. Start with something more fun and lighthearted, like, “What’s your most embarrassing holiday story?” or “If you could bring one celebrity to dinner, who would it be and why?” Trust me, these questions lead to better stories than talking about your job for the 17th time.

Survival Tip #4: A Little Holiday Romance Never Hurt Anyone

The holidays are a great time for romance. Seriously, if there was ever a season made for cozying up with someone special, it's now. But let’s face it: holiday romance can feel like a double-edged sword. On one hand, there’s something magical about the twinkling lights and chilly air. On the other, you might find yourself questioning if that sweet text from someone is a sign of genuine interest—or just a little bit of holiday fluff.

Here’s the trick: Keep dating during the holidays low-pressure, but make it memorable. Forget the formal dinner reservations (because, seriously, who needs another overly-starched meal at a candlelit restaurant?). Instead, go for something fun and festive—think hot chocolate at a quirky café or ice skating under the lights. It’s all about sharing an experience, not just sitting there. 

Survival Tip #5: Avoiding the “Holiday Hookup Hangover” 

Holiday parties bring a certain... energy. The drinks are flowing, people are feeling festive, and, well, sometimes it leads to an unexpected holiday hookup. Now, we’re not here to shame anyone who enjoys a little holiday fun, but let’s be real: not everyone wants to wake up with a “what happened last night?” moment.

Pro Tip:  Be mindful of your intentions. If it’s a one-time fling, own it! But if you’re not into the casual hookup scene, it’s okay to politely pass on the mistletoe action. And make sure to stay safe and keep it respectful. Ensure both you and your partner are on the same page, whether it’s just a fun night or something more. No one likes the confusion that can follow after a drunken “under the mistletoe” moment.

Survival Tip #6: Handling the "Ex-Factor"

Now this is niché, but nothing says ‘Tis the Season like accidentally running into your ex at a holiday party. Maybe it’s the nostalgia, maybe it’s the eggnog, but this situation has all the potential for awkwardness.

Pro Tip: Repeat after me… Smile, say hi, and keep it brief. You’re here to enjoy the party, not rehash the past. For the love of all that’s good and holy, resist the temptation to prove you’re “winning” the breakup. Your genuine happiness and indifference towards them is the best flex. And if all else fails (and if you brought a friend) let them know you might need a little backup to gracefully exit the conversation, or the party. 

Survival Tip #7:  Keep It Chill, Keep It Fun & Set Healthy Boundaries

At the end of the day, the holiday season is meant to be fun, and the same should go for your dating life. Remember that the best connections come from being real. However we also know that dating during the holidays can bring up a lot of emotions and expectations. So it’s also important to remember that it’s okay to set boundaries. If you're overwhelmed by all the events, don’t be afraid to take a break or say no to certain invites. Remember, your time and energy are valuable and being upfront about that will save you a lot of stress later on.

Survival Tip #8: End-of-Year Reflections

The holiday season often brings with it a flurry of excitement. But it’s also the perfect time to hit pause and reminisce on the year that’s coming to a close. The end of the year is the ultimate time to reflect not only on how far you’ve come but also on what worked, what didn’t, and what you want to take with you into the new year. Have you been intentional with your dating life, or have you been going through the motions? Were you focusing on your needs, or were you compromising too much? It’s a chance to reset, recalibrate, and learn from the moments that made you smile and the moments that made you question your choices.

With a little intentionality, humor, and FROM by your side, you can not only survive but thrive this holiday season. Whether you're single, mingling, or dating with purpose, there’s no reason why this can’t be your best season of love yet. So, go ahead—pour yourself a glass of wine (or hot cocoa), embrace the awkward moments with a laugh, and soak up the magic of the holidays. Who knows? You might just find love under the mistletoe... or at least collect a few hilarious stories to share. Happy Holidays, and happy dating! 💖

HJF for First Round’s On Me